As a 15 year old, Ramesh Sippy plays an antagonistic street urchin named Jaggu Dada in Bhai-Bahen (1959), directed and produced by his father.

He was sent to London for higher studies, but dropped out and came back to join his father's production house. Works as an assistant in the production and direction departments for his father's films, including Mere Sanam (1965) and Brahmachari (1968), on which he was the executive producer. This seven-year apprenticeship serves as his film school.

Ramesh Sippy debuts with Andaz, a risky subject about a widow (Hema Malini) and a widower (Shammi Kapoor) finding love. It was inspired from Un homme et une femme (1966), proved to be a resounding box-office success, and established Ramesh as a filmmaker to watch out for. The "Sippy Films Writing Department" included two budding film writers, Salim Khan and Javed Akhtar.

Seeta Aur Geeta was the remake of Ram Aur Shyam with a gender twist. It propelled Hema Malini to superstardom and won her the Filmfare Best Actress award.

Originally a 4-line idea about two army men, Sholay eventually changed to two thieves hired to nab a bandit ​. The story was conceived by Salim and Javed, once part of his own wrting team. By this time, the two had made a name of their own. The film was as much a technological triumph as it was a storytelling one. It introduced 70mm and stereophonic sound to India. Though critics initially panned it, it ran for five years in theaters and became a veritable classic. It had the longest running record in Indian cinemas before DIlwaale Dulhaniya Le Jayenge broke it. Cataputled Amjad Khan to instant stardom and etched Gabbar Singh as the quintessential Hindi film villain. Became the high watermark for Bollywood blockbusters, still considered one of the biggest Indian films ever made.

Attempting to move away from the rustic setting of Sholay, Ramesh Sippy created an urban, gadget-heavy action thriller in Shaan. The suave Shakaal was an antithesis to Gabbar SIngh and despite Kulbhushan Kharbanda's compelling performance as the antagonist, the role didn't catch on at all. The film did attain some amount of commercial success but was considered a disappointment relative to Sholay's massive expectations ​.

Ramesh Sippy pulled off a veritable casting coup by casting the tragedy king (Dilip Kumar) and the angry young man (Bachchan) as father and son. A critical favorite, Shakti won the Filmfare Best Movie award but was only a modest commercial success, despite the impeccable performances.

Saagar's achievemnet was its casting - Dimple Kapadia in her comeback role after her marriage and sabbatical, and for casting Kamal Haasan in a powerful, author-backed role. The film was India's official entry for the Academy Award for Best Foreign Language Film. Despite some credible acting work, the film bombed at the box-office. Its music outlived the film.

Directs Buniyad (1987) for Indian television. Written by Manohar Shyam Joshi, the show dealt with the Partition of India—a subject close to Sippy's own history. It became a cultural phenomenon, emptying streets during its telecast, similar to what happened during the serials Ramayan and Mahabharat. Directs Bhrashtachar (1989). A crime drama starring Mithun Chakraborty and Rekha, followed by Akayla (1991), in which her co-star was Amitabh Bachchan. Despite the star power and the team working in favour of the film, it was a commercial failure. Next project, Zamana Deewana (1995) starring Shah Rukh Khan and Raveena Tandon tanked without a trace. Ramesh Sippy decides to hang up his boots.

For nearly two decades, Sippy put down the director's baton and focused on producing films, often launching his son Rohan Sippy.

2003: Produces Kuch Naa Kaho (Directed by son Rohan Sippy).

2005: Produces Bluffmaster! (Sttarring Abhishek Bachchan).

2006–2011: Produces a string of films including Taxi No. 9211 (2006), Chandni Chowk to China (2009), and Dum Maaro Dum (2011).​

2013: Awarded the Padma Shri, India's fourth-highest civilian honour, for his contribution to cinema.​

2017: Founded the Ramesh Sippy Academy of Cinema & Entertainment (RSACE) in Mumbai to train aspiring filmmakers.